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Welcome to Ask Different! Questions about development, Apple developer programs, iTunes Connect, and listing your apps on the App Store are off-topic for this site. Please take a look at the FAQs for more info. Thanks.
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Nathan GreensteinOct 8 '11 at 20:18

2 Answers
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If you want to develop HTML5 web apps that run in Safari on your Mac/iPhone/iPad, it's free. These apps can be designed as web clippings for your device as well.

If you want to develop Simulated iOS apps that run on the iPhone/iPad Simulator on a Mac, it's free (after the cost of your Intel Mac with Snow Leopard or Lion), or maybe $5 to download the tools from the Mac App store.

If you want to develop, install and run a native iOS app on any stock OS iPhone or iPad, you need to pay $99/annum to enroll in Apple's iOS Developer program.

If you want to submit a native app or an app encapsulated HTML5 web app to Apple's iTunes App store, you need to be enrolled in the same $99 per year iOS Developer program.

If your app is a paid app that they approve for distribution from their App store, Apple pays you around 70% of what it charges the customers (less if there's a VAT tax).

There is a $99/year fee to be a member of the development program. If you are not a member, you can download Xcode and SDKs for publicly released versions of iOS and work on your apps, but you will only be able to run them in the simulator. If you want to be able to run the app on an actual device or enter it into the app store, you need to be a member. If your app is not free, or uses in-app purchases, Apple keeps 30% of any sales.